Copper-catalyzed silylation of p-quinone methides: new entry to dibenzylic silanes
نویسندگان
چکیده
منابع مشابه
Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates
In this report, we establish that DM-Segphos copper(I) complexes are efficient catalysts for the enantioselective borylation of para-quinone methides. This method provides straightforward access to chiral monobenzylic and dibenzylic boronic esters, with enantiomeric ratios up to 96:4, using a commercially available chiral phosphine. Standard manipulations of the C-B bond afford a variety of chi...
متن کاملCopper-catalyzed silylation of p-quinone methides: new entry to dibenzylic silanes† †Electronic supplementary information (ESI) available: Experimental details, characterization and crystallographic data. CCDC 1414585. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5cc06653k Click here for additional data file. Click here for additional data file.
3. General procedure for synthesis of
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Presented is the first enantioselective copper-catalyzed 1,6-conjugate addition of bis(pinacolato)diboron to para-quinone methides. The reaction proceeds with excellent yields and good to excellent enantioselectivities, and provides an attractive approach to the construction of optically active gem-diarylmehtine boronic esters. Additionally, the subsequent conversion of the derived potassium tr...
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A variety of cyclopropenes undergo direct silylation using (trifluoromethyl)trimethylsilane in the presence of a copper-bisphosphine catalyst; under these conditions, cyclopropenes that might otherwise undergo ring-opening are silylated efficiently.
متن کاملThe Domestication of ortho-Quinone Methides
CONSPECTUS: An ortho-quinone methide (o-QM) is a highly reactive chemical motif harnessed by nature for a variety of purposes. Given its extraordinary reactivity and biological importance, it is surprising how few applications within organic synthesis exist. We speculate that their widespread use has been slowed by the complications that surround the preparation of their precursors, the harsh g...
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ژورنال
عنوان ژورنال: Chemical Communications
سال: 2015
ISSN: 1359-7345,1364-548X
DOI: 10.1039/c5cc06653k